A traditional single-item clipboard stores a single most-recently copied content item. The clipboard retrieves that content item when the user activates a paste command. A multi-item clipboard, on the other hand, can store plural content items. While a multi-item clipboard is more versatile than a traditional clipboard, it is also more complex; this complexity introduces various technical challenges, both in the design of the multi-item clipboard, as well as the mechanisms by which applications interact with the multi-item clipboard.